Carphenazine

Identification

Generic Name
Carphenazine
DrugBank Accession Number
DB01038
Background

Carphenazine is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.

Type
Small Molecule
Groups
Withdrawn
Structure
Weight
Average: 425.59
Monoisotopic: 425.213698424
Chemical Formula
C24H31N3O2S
Synonyms
  • Carfenazina
  • Carfenazine
  • Carfénazine
  • Carfenazinum
  • Carphenazine

Pharmacology

Indication

Used in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Carphenazine is a phenothiazine antipsychotic agent with a piperazine side-chain.

Mechanism of action

A yellow, powdered, phenothiazine antipsychotic agent used in the treatment of acute or chronic schizophrenia. The term "phenothiazines" is used to describe the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as akathisia, tardive dyskinesia and extrapyramidal symptoms. Carphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
ADopamine D1 receptor
antagonist
Humans
ADopamine D5 receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
ApomorphineThe therapeutic efficacy of Apomorphine can be decreased when used in combination with Carphenazine.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Carphenazine.
BenzatropineThe risk or severity of adverse effects can be increased when Carphenazine is combined with Benzatropine.
BrexpiprazoleThe therapeutic efficacy of Brexpiprazole can be decreased when used in combination with Carphenazine.
BromocriptineThe therapeutic efficacy of Bromocriptine can be decreased when used in combination with Carphenazine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Carphenazine maleate0HX1Z0A2MC2975-34-0TVPJGGZLZLUPOB-SPIKMXEPSA-N
International/Other Brands
Proketazin / Proketazine (Wyeth)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Aryl alkyl ketones / N-alkylpiperazines / Benzenoids / 1,4-thiazines / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols
show 3 more
Substituents
1,2-aminoalcohol / 1,4-diazinane / Alcohol / Alkanolamine / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Aryl thioether
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
CLY16Y8Z7E
CAS number
2622-30-2
InChI Key
XZSMZRXAEFNJCU-UHFFFAOYSA-N
InChI
InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
IUPAC Name
1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
SMILES
CCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1

References

Synthesis Reference

Tislow, R.F., Bruce, W.F. and Page, J.A.; US. Patent 3,023,146; February 27,1962; assigned to American Home Products Corporation. Sherlock, M.H. and Sperber, N.; US. Patent 2,985,654; May 23, 1961; assigned to Schering Corporation.

US3023146
General References
Not Available
Human Metabolome Database
HMDB15172
PubChem Compound
18104
PubChem Substance
46505936
ChemSpider
17100
ChEBI
51235
ChEMBL
CHEMBL1201328
ZINC
ZINC000022446644
Therapeutic Targets Database
DAP000846
PharmGKB
PA164750571
Wikipedia
Carfenazine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)175-177Tislow, R.F., Bruce, W.F. and Page, J.A.; US. Patent 3,023,146; February 27,1962; assigned to American Home Products Corporation. Sherlock, M.H. and Sperber, N.; US. Patent 2,985,654; May 23, 1961; assigned to Schering Corporation.
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0366 mg/mLALOGPS
logP3.26ALOGPS
logP3.35Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.56Chemaxon
pKa (Strongest Basic)7.67Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area47.02 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity126.32 m3·mol-1Chemaxon
Polarizability49.22 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9651
Caco-2 permeable-0.5189
P-glycoprotein substrateSubstrate0.8797
P-glycoprotein inhibitor IInhibitor0.8874
P-glycoprotein inhibitor IINon-inhibitor0.5543
Renal organic cation transporterNon-inhibitor0.5663
CYP450 2C9 substrateNon-substrate0.7229
CYP450 2D6 substrateSubstrate0.6853
CYP450 3A4 substrateNon-substrate0.665
CYP450 1A2 substrateInhibitor0.7862
CYP450 2C9 inhibitorNon-inhibitor0.9027
CYP450 2D6 inhibitorInhibitor0.8766
CYP450 2C19 inhibitorNon-inhibitor0.7951
CYP450 3A4 inhibitorNon-inhibitor0.6655
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5559
Ames testNon AMES toxic0.8058
CarcinogenicityNon-carcinogens0.8774
BiodegradationNot ready biodegradable0.9848
Rat acute toxicity2.6455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8272
hERG inhibition (predictor II)Inhibitor0.7613
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0010900000-d86dc6841f760f4bf205
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-220bb92f0e7145fd6454
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0160900000-2621ce9b1557242397e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-0009400000-57608800a18871fa0e3a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006t-1509100000-24ba46fbfc8782e059c9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ug3-3159000000-0d2acf9134721f8c5889
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-197.84093
predicted
DeepCCS 1.0 (2019)
[M+H]+200.1989
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.02301
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [Article]
  2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
  3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  5. CARPHENAZINE [Link]
  6. CHEBI:51235 - carphenazine [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [Article]
  2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
  3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD5
Uniprot ID
P21918
Uniprot Name
D(1B) dopamine receptor
Molecular Weight
52950.5 Da
References
  1. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [Article]
  2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
  3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:54